Triethylamine → HCID 19771064, compound

HRID 1589867Notes

Reaction equation

HRID 1589867 reaction equation
[NH2:1][C:2]1[CH:16]=[C:15]([C:17]([F:20])([F:19])[F:18])[CH:14]=[CH:13][C:3]=1[NH:4][C:5]1[CH:10]=[C:9]([Cl:11])[CH:8]=[CH:7][C:6]=1[OH:12].C(N(CC)CC)C.[C:28](C1NC=CN=1)(C1NC=CN=1)=[S:29]>O1CCCC1>[Cl:11][C:9]1[CH:8]=[CH:7][C:6]([OH:12])=[C:5]([N:4]2[C:3]3[CH:13]=[CH:14][C:15]([C:17]([F:20])([F:18])[F:19])=[CH:16][C:2]=3[NH:1][C:28]2=[S:29])[CH:10]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 11412697Thiocarbonyl diimidazoleHCID 19771130HCID 19771130, compound

Product 1

HCID 19771064HCID 19771064, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2-amino-N-(5-chloro-2-hydroxyphenyl)-4-trifluoromethyl-aniline (0.51 g, 1 5 mmol), triethylamine (0.28 ml, 2 mmol) and thiocarbonyl diimidazol (0.36 g, 2 mmol) was dissolved in dry tetrahydrofuran (15 ml) and the mixture was stirred for 30 minutes. The reaction mixture was evaporated in vacuo. The residue was redissolved in ethanol and water and light petroleum were added. The precipitate was isolated and was purified by column chromatography on silica gel with ether/light petroleum (2:1) as eluent. Yield of title compound was 200 mg, M.p. 248°-250° C.

Workup

  1. customThe reaction mixture was evaporated in vacuo
  2. dissolutionThe residue was redissolved in ethanol
  3. additionwater and light petroleum were added
  4. customThe precipitate was isolated
  5. customwas purified by column chromatography on silica gel with ether/light petroleum (2:1) as eluent

Sources & evidence

ORD record
ord-78e515c28ed14b23ba5d870b9794db4d
Source dataset
uspto-grants-1993_04
Patent number
US05200422

Reaction notes

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